Transparent resin and plastic lens

ABSTRACT

A transparent resin obtained by polymerizing a monomer having an alkylene oxide group, a polyfunctional (meth)acrylate having a divalent branched hydrocarbon group and other copolymerizable vinyl monomer, if necessary, is suitable as an elementary material for a plastic lens with excellent heat resistance and hue.

BACKGROUND OF THE INVENTION

The present invention relates to a transparent resin utilizable as anelementary material of plastic lens, a process for production of saidresin, a plastic lens, and a casting composition for production of thetransparent resin.

As a material of optical lenses, resins of high transparency such asacrylic resin, diethylene glycol bis-allylcarbonate resin (for example,CR-39), polystyrene, polycarbonate and the like have hitherto been used.Of these resins, diethylene glycol bis-allylcarbonate resin which is athermosetting resin is most extensively used as a material of eyeglasslens. This is due to the high transparency, low dispersibility (highAbbe number) and excellence in heat and impact resistances.

However, a lens made of diethylene glycol bis-allylcarbonate isdisadvantageous in that its refractive index is as low as 1.50 and itsthickness is unavoidably greater than that of a lens made of glass (thistendency becomes more marked as thickness of lens increases). Further,this type of lens is inferior in abrasion resistance, like generalplastic lenses. Although a method of coating the surface of this type oflens with an organosilane type hard coat film has been proposed in orderto overcome this disadvantage, an untreated plastic lens is insufficientin adhesive strength to the organosilane type hard coat film and cannotmake a uniform adhesion. In other words, the organosilane type hard coatcan be formed only after treating the surface of plastic lens.

Further, it is an increasing demand of the time to reduce the weight ofeyeglass, so that material of low specific gravity for production ofeyeglass is actively being studied. For example, Japanese PatentUnexamined Publication No. (JP-A) 2-238006 has proposed acrylic resinsusing 2,2-dialkyl-1,3-propane-di(meth)acrylate. This material, however,is unsatisfactory because its specific gravity is so high as about 1.31to 1.35 and this material is inferior in dyeability and adhesiveness toorganosilane type hard coat film. In JP-A-5-215903, there has beenproposed a copolymer constituted of [di(meth)acrylate having straightchain alkyl group as spacer]/[(meth)acrylate having alkylgroup]/aromatic vinyl compound/other monomer. Although this material hasa low specific gravity, it is readily deformable in the process ofdyeing and hard coating due to its low heat resistant temperature.Further, all the materials mentioned above are insufficient in strengthso that they are readily breakable in the course of boring process.

JP-A-4-126710 has proposed a copolymer constituted of [alkylene oxidegroup-containing bifunctional (meth)acrylate]/[aromatic vinylmonomer]/[polymerizable monomer or polymerizable oligomer having apolymerizable double bond and a molecular weight of 98 or above].However, this material is yet insufficient in the lowness of specificgravity and its hue tends to become yellowish.

Further, as resins improved in the adhesive property to hard coat film,a copolymer constituted of [aromatic ring-containingdi(meth)acrylate]/[aromatic ring-containing monomer]/[hydroxylgroup-containing monomer] (JP-A-58-76410) and a copolymer constituted of[aromatic ring-containing di(meth)acrylate]/[aromatic ring-containingmonomer]/[epoxy group-containing monomer] (JP-A-58-89606) have beenproposed. These materials, however, are yet unsatisfactory in theadhesive property to organosilane type hard coat film, even thoughadhesion to glass film after glass vapor deposition is improved.Further, the latter resin is undesirable from the viewpoint ofmoldability because its adhesiveness to glass mold used in castpolymerization process excessively increases as the proportion of epoxygroup-containing monomer in the copolymer increases.

As has been mentioned above, there has hitherto been disclosed noplastic lens nor resin for plastic lens which is excellent in hue andwell-balanced between strength at the time of boring processing andspecific gravity, has the properties required of a plastic lens, and candirectly be coated with an organosilane type hard coat film withoutsurface treatment.

SUMMARY OF THE INVENTION

It is an object of the present invention to provide a transparent resinexcellent in the hue and well-balanced between strength at the time ofboring processing and specific gravity, a process for producing saidtransparent resin, a plastic lens made of said transparent resin, and acasting composition for production of the transparent resin. It isanother object of the present invention to provide a transparent resinwhich has a low dispersibility (high Abbe number), a high refractiveindex, an excellent dyeing property and a high heat resistance inaddition to the above-mentioned characteristic properties, a process forproducing said transparent resin, and a plastic resin made of saidtransparent resin. It is a further object of the present invention toprovide a transparent resin which can directly be coated with anorganosilane type hard coat film without surface treatment, a processfor producing said transparent resin, and a plastic lens made of saidtransparent resin.

The present invention provides a transparent resin comprising, asconstituent components of the resin molecules, a polymerizable monomermixture obtained by compounding:

1 to 80 parts by weight of an alkylene oxide group-containing monomerrepresented by the following general formula (I):

    R.sup.1 --O--(R.sup.2 O).sub.n --R.sup.3                   (I)

wherein R¹ is an acryloyl group or a methacryloyl group; R² is analkylene group having 1 to 5 carbon atoms; R³ is a hydrogen atom, anacryloyl group, a methacryloyl group or a monovalent hydrocarbon groupother than those mentioned above and having 1 to 40 carbon atoms; and nis an integer of 9 to 50;

1 to 95 parts by weight of a polyfunctional (meth)acrylate representedby the following general formula (II): ##STR1## wherein R⁴ and R⁵ areindependently an acryloyl group or a methacryloyl group; and R⁶ and R⁷are independently a monovalent hydrocarbon group having 1 to 6 carbonatoms; and

0 to 90 parts by weight of other copolymerizable vinyl monomer,

so that total amount of monomers comes to 100 parts by weight.

Further, the present invention provides a process for producing atransparent resin which comprises polymerizing the polymerizable monomermixture mentioned above.

The transparent resin has desirably a specific gravity of 1.15 or below,a refractive index of 1.54 or above and an Abbe number of 35 or above.Furthermore, the transparent resin in the invention has a specificgravity of 1.05 or above, a refractive index of 1.57 or below and anAbbe number of 50 or below in many case.

Furthermore, the present invention provides a plastic lens obtained fromthe transparent resin mentioned above.

DESCRIPTION OF THE PREFERRED EMBODIMENTS

The alkylene oxide group-containing monomer used for production of thetransparent resin of the present invention is represented by the formula(I):

    R.sup.1 --O--(R.sup.2 O).sub.n --R.sup.3                   (I)

wherein R¹ is an acryloyl group or a methacryloyl group; R² is analkylene group having 1 to 5 carbon atoms; R³ is a hydrogen atom, anacryloyl group, a methacryloyl group or a monovalent hydrocarbon groupother than those mentioned above and having 1 to 40 carbon atoms; and nis an integer of 9 to 50.

The alkylene oxide group-containing monomers represented by theabove-mentioned formula (I) include monofunctional monomers andpolyfunctional monomers.

Among the alkylene oxide group-containing monomers represented by theabove-mentioned formula (I), the monofunctional monomers include:

polymethylene glycol monoacrylates such as nonamethylene glycolmonoacrylate, tridecamethylene glycol monoacrylate, tetradecamethyleneglycol monoacrylate, tricosamethylene glycol monoacrylate and the like;

polymethylene glycol monomethacrylates such as nonamethylene glycolmonomethacrylate, tridecamethylene glycol monomethacrylate,tetradecamethylene glycol monomethacrylate, tricosamethylene glycolmonomethacrylate and the like;

alkoxypolymethylene glycol acrylates such as methoxynonamethylene glycolacrylate, methoxytridecamethylene glycol acrylate,methoxytetradecamethylene glycol acrylate, methoxytricosamethyleneglycol acrylate, ethoxynonamethylene glycol acrylate,ethoxytridecamethylene glycol acrylate, ethoxytetradecamethylene glycolacrylate, ethoxytricosamethylene glycol acrylate and the like;

alkoxypolymethylene glycol methacrylates such as methoxynonamethyleneglycol methacrylate, methoxytridecamethylene glycol methacrylate,methoxytetradecamethylene glycol methacrylate, methoxytricosamethyleneglycol methacrylate, ethoxynonamethylene glycol methacrylate,ethoxytridecamethylene glycol methacrylate, ethoxytetradecamethyleneglycol methacrylate, ethoxytricosamethylene glycol methacrylate and thelike;

polyethylene glycol monoacrylates such as nonaethylene glycolmonoacrylate, tridecaethylene glycol monoacrylate, tetradecaethyleneglycol monoacrylate, tricosaethylene glycol monoacrylate and the like;

polyethylene glycol monomethacrylates such as nonaethylene glycolmonomethacrylate, tridecaethylene glycol monomethacrylate,tetradecaethylene glycol monomethacrylate, tricosaethylene glycolmonomethacrylate and the like;

alkoxypolyethylene glycol acrylates such as methoxynonaethylene glycolacrylate, methoxytridecaethylene glycol acrylate,methoxytetradecaethylene glycol acrylate, methoxytricosaethylene glycolmonoacrylate, ethoxynonaethylene glycol acrylate, ethoxytridecaethyleneglycol acrylate, ethoxytetradecaethylene glycol acrylate,ethoxytricosaethylene glycol acrylate and the like;

alkoxypolyethylene glycol methacrylates such as methoxynonaethyleneglycol methacrylate, methoxytridecaethylene glycol methacrylate,methoxytetradeca ethylene glycol methacrylate, methoxytricosaethyleneglycol methacrylate, ethoxynonaethylene glycol methacrylate,ethoxytridecaethylene glycol methacrylate, ethoxytetradecaethyleneglycol methacrylate, ethoxytricosaethylene glycol methacrylate and thelike;

polypropylene glycol monoacrylates such as nonapropylene glycolmonoacrylate, dodecapropylene glycol monoacrylate, tridecapropyleneglycol monoacrylate and the like;

polypropylene glycol monomethacrylates such as nonapropylene glycolmonometharylate, dodecapropylene glycol monomethacrylate,tridecapropylene glycol monomethacrylate and the like;

alkoxypolypropylene glycol acrylates such as methoxynonapropylene glycolacrylate, methoxydodecapropylene glycol acrylate,methoxytridecapropylene glycol acrylate, ethoxynonapropylene glycolacrylate, ethoxydodecapropylene glycol acrylate, ethoxytridecapropyleneglycol acrylate and the like;

alkoxypolypropylene glycol methacrylates such as methoxynonapropyleneglycol methacrylate, methoxydodecapropylene glycol methacrylate,methoxytridecapropylene glycol methacrylate, ethoxynonapropylene glycolmethacrylate, ethoxydodecapropylene glycol methacrylate,ethoxytridecapropylene glycol methacrylate and the like;

polybutylene glycol monoacrylates such as nonabutylene glycolmonoacrylate, dodecabutylene glycol monoacrylate, tridecabutylene glycolmonoacrylate and the like;

polybutylene glycol monomethacrylates such as nonabutylene glycolmonomethacrylate, dodecabutylene glycol monomethacrylate,tridecabutyleneglycol monomethacrylate and the like;

alkoxypolybutylene glycol acrylates such as methoxynonabutylene glycolacrylate, methoxydodecabutylene glycol acrylate, methoxytridecabutyleneglycol acrylate, ethoxynonabutylene glycol acrylate,ethoxydodecabutylene glycol acrylate, ethoxytridecabutylene glycolacrylate and the like;

alkoxypolybutylene glycol methacrylates such as methoxynonabutyleneglycol methacrylate, methoxydodecabutylene glycol methacrylate,methoxytridecabutylene glycol methacrylate, ethoxynonabutylene glycolmethacrylate, ethoxydodecabutylene glycol methacrylate,ethoxytridecabutylene glycol methacrylate and the like;

polyethylene glycol polypropylene glycol monoacrylates such asheptaethylene glycol tripropylene glycol monoacrylate, nonaethyleneglycol propylene glycol monoacrylate, tetraethylene glycol propyleneglycol monoacrylate, nonaethylene glycol dipropylene glycolmonoacrylate, tetradecaethylene glycol dipropylene glycol monoacrylate,nonaethylene glycol tripropylene glycol monoacrylate, tetradecaethyleneglycol tripropylene glycol monoacrylate and the like;

polyethylene glycol polypropylene glycol monomethacrylates such asheptaethylene glycol tripropylene glycol monomethacrylate, nonaethyleneglycol propylene glycol monomethacrylate, tetradecaethylene glycolpropylene glycol monomethacrylate, nonaethylene glycol dipropyleneglycol monomethacrylate, tetradecaethylene glycol dipropylene glycolmonomethacrylate, nonaethylene glycol tripropylene glycolmonomethacrylate, tetradecaethylene glycol tripropylene glycolmonomethacrylate and the like;

polyethylene glycol polybutylene glycol monoacrylates such asdecaethylene glycol pentabutylene glycol monoacrylate and the like;

polyethylene glycol polybutylene glycol monomethacrylates such asdecaethylene glycol pentabutylene glycol monomethacrylate and the like;etc. These monomers are used either in the form of single monomer or inthe form of a mixture of two or yore.

Among the alkylene oxide group-containing monomers represented by theformula (I), polyfunctional monomers include the following:

polymethylene glycol diacrylates such as nonamethylene glycoldiacrylate, tridecamethylene glycol diacrylate, tetradecamethyleneglycol diacrylate, tricosamethylene glycol diacrylate and the like;

polymethylene glycol dimethacrylates such as nonamethylene glycoldimethacrylate, tridecamethylene glycol dimethacrylate,tetradecamethylene glycol dimethacrylate, tricosamethylene glycoldimethacrylate and the like;

polyethylene glycol diacrylates such as nonaethylene glycol diacrylate,tridecaethylene glycol diacrylate, tetradecaethylene glycol diacrylate,tricosaethylene glycol diacrylate and the like;

polyethylene glycol dimethacrylates such as nonaethylene glycoldimethacrylate, tridecaethylene glycol dimethacrylate, tetraethyleneglycol dimethacrylate, tricosaethylene glycol dimethacrylate and thelike;

polypropylene glycol diacrylates such as nonapropylene glycoldiacrylate, dodecapropylene glycol diacrylate, tridecapropylene glycoldiacrylate and the like;

polypropylene glycol dimethacrylates such as nonapropylene glycoldimethacrylate, dodecapropylene glycol dimethacrylate, tridecapropyleneglycol dimethacrylate and the like;

polybutylene glycol diacrylates such as nonabutylene glycol diacrylate,dodecabutylene glycol diacrylate, tridecabutylene glycol diacrylate andthe like;

polybutylene glycol dimethacrylates such as nonabutylene glycoldimethacrylate, dodecabutylene glycol dimethacrylate, tridecabutyleneglycol dimethacrylate and the like;

polyethylene glycol polypropylene glycol diacrylates such asheptaethylene glycol tripropylene glycol diacrylate, nonaethylene glycolpropylene glycol diacrylate, tetraethylene glycol propylene glycoldiacrylate, nonaethylene glycol dipropylene glycol diacrylate,tetradecaethylene glycol dipropylene glycol diacrylate,tetradecaethylene glycol tripropylene glycol diacrylate and the like;

polyethylene glycol polypropylene glycol dimethacrylates such asheptaethylene glycol tripropylene glycol dimethacrylate, nonaethyleneglycol propylene glycol dimethacrylate, tetradecaethylene glycolpropylene glycol dimethacrylate, nonaethylene glycol dipropylene glycoldimethacrylate, tetradeca- ethylene glycol dipropylene glycoldimethacrylate, nonaethylene glycol tripropylene glycol dimethacrylate,tetradecaethylene glycol tripropylene glycol dimeth- acrylate and thelike;

polyethylene glycol polybutylene glycol diacrylates such as decaethyleneglycol pentabutylene glycol diacrylate and the like;

polyethylene glycol polybutylene glycol dimethacrylates such asdecaethylene glycol pentabutylene glycol dimethacrylate and the like;etc. These monomers are used either in the form of a single monomer orin the form of a mixture of two or more monomers.

Among the monomers exemplified above, the following polyfunctionalmonomers are preferred as the alkylene oxide group-containing monomerrepresented by the formula (I) from the viewpoint of hue and heatresistance:

polymethylene glycol diacrylates such as nonamethylene glycoldiacrylate, tridecamethylene glycol diacrylate, tetradecamethyleneglycol diacrylate, tricosamethylene glycol diacrylate and the like;

polymethylene glycol dimethacrylates such as nonamethylene glycoldimethacrylate, tridecamethylene glycol dimethacrylate,tetradecamethylene glycol methacrylate, tricosamethylene glycoldimethacrylate and the like;

polyethylene glycol diacrylates such as nonaethylene glycol diacrylates,tridecaethylene glycol diacrylate, tetradecaethylene glycol diacrylate,tricosaethylene glycol diacrylate and the like;

polyethylene glycol dimethacrylates such as nonaethylene glycoldimethacrylate, tridecaethylene glycol dimethacrylate, tetradecaethyleneglycol dimethacrylate, tricosaethylene glycol dimethacrylate and thelike;

polypropylene glycol diacrylates such as nonapropylene glycoldiacrylate, dodecapropylene glycol diacrylate, tridecapropylene glycolacrylate and the like;

polypropylene glycol dimethacrylates such as nonapropylene glycoldimethacrylate, dodecapropylene glycol dimethacrylate, tridecapropyleneglycol dimethacrylate and the like;

polybutylene glycol diacrylates such as nonabutylene glycol diacrylate,dodecabutylene glycol diacrylate, tridecabutylene glycol diacrylate andthe like;

polybutylene glycol dimethacrylates such as nonabutylene glycoldimethacrylate, dodecabutylene glycol dimethacrylate, tridecabutyleneglycol dimethacrylate and the like;

polyethylene glycol polypropylene glycol diacrylates such asheptaethylene glycol tripropylene glycol diacrylate, nonaethylene glycolpropylene glycol diacrylate, tetradecaethylene glycol propylene glycoldiacrylate, nonaethylene glycol dipropylene glycol diacrylate,tetradecaethylene glycol dipropylene glycol diacrylate, nonaethyleneglycol tripropylene glycol diacrylate, tetradecaethylene glycoltripropylene glycol diacrylate and the like;

polyethylene glycol polypropylene glycol dimethacrylates such asheptaethylene glycol tripropylene glycol dimethacrylate, nonaethyleneglycol propylene glycol dimethacrylate, tetradecaethylene glycolpropylene glycol dimethacrylate, nonaethylene glycol dipropylene glycoldimethacrylate, tetradecaethylene glycol dipropylene glycoldimethacrylate, nonaethylene glycol tripropylene glycol dimethacrylate,tetradecaethylene glycol tripropylene glycol dimethacrylate and thelike;

polyethylene glycol polybutylene glycol diacrylates such as decaethyleneglycol pentabutylene glycol diacrylate and the like;

polyethylene glycol polybutylene glycol dimethacrylates such asdecaethylene glycol pentabutylene glycol dimethacrylate and the like;etc.

Among the monomers exemplified above, polyalkylene glycoldi(meth)acrylates of which alkylene oxide group has 2 to 3 carbon atomssuch as those mentioned below are further preferable from the viewpointof adhesive property to organosilane type hard coat film and dyeability:

polyethylene glycol diacrylates such as nonaethylene glycol diacrylate,tridecaethylene glycol diacrylate, tetradecaethylene glycol diacrylate,tricosaethylene glycol diacrylate and the like;

polyethylene glycol dimethacrylates such as nonaethylene glycoldimethacrylate, tridecaethylene glycol dimethacrylate, tricosaethyleneglycol dimethacrylate and the like;

polypropylene glycol diacrylates such as nonapropylene glycoldiacrylate, dodecapropylene glycol diacrylate, tridecapropylene glycoldiacrylate and the like;

polypropylene glycol dimethacrylates such as nonapropylene glycoldimethacrylate, dodecapropylene glycol dimethacrylate, tridecapropyleneglycol dimethacrylate and the like;

polyethylene glycol polypropylene glycol diacrylates such asheptaethylene glycol tripropylene glycol diacrylate, nonaethylene glycolpropylene glycol diacrylate, tetradecaethylene glycol propylene glycoldiacrylate, nonaethylene glycol dipropylene glycol diacrylate,tetradecaethylene glycol dipropylene glycol diacrylate, nonaethyleneglycol tripropylene glycol diacrylate, tetradecaethylene glycoltripropylene glycol diacrylate and the like;

polyethylene glycol polypropylene glycol dimethacrylates such asheptaethylene glycol tripropylene glycol dimethacrylate, nonaethyleneglycol propylene glycol dimethacrylate, tetradecaethylene glycolpropylene glycol dimethacrylate, nonaethylene glycol dipropylene glycoldimethacrylate, tetradecaethylene glycol dipropylene glycoldimethacrylate, nonaethylene glycol tripropylene glycol dimethacrylate,tetradecaethylene glycol tripropylene glycol dimethacrylate and thelike; etc.

Among the monomers exemplified above, tetradecaethylene glycoldi(meth)acrylate is particularly preferable from the viewpoint of hueand the balance between strength at the time of boring processing,dyeability, heat resistance and adhesiveness to organosilane type hardcoat film.

Preferably, the alkylene oxide group-containing monomer represented bythe formula (I) is used in an amount of 1 to 80 parts by weight per 100parts by weight of the total monomers. If its amount is smaller than 1part by weight, the strength at the time of boring processing and thedyeability are apt to deteriorate, and the adhesiveness to organosilanetype hard coat is apt to deteriorate. If the amount of monomer (I) isgreater than 80 parts by weight, heat resistance is apt to deteriorate,hue is apt to become yellowish, and specific gravity is too high.

For sufficiently improving the strength at the time of boringprocessing, the dyeability and the adhesiveness to organosilane typehard coat film, it is necessary to use the alkylene oxidegroup-containing monomer represented by the formula (I) in an amount ofat least 5 parts by weight per 100 parts by weight of total monomers.Further, for preventing deterioration of heat resistance, yellowing ofhue and increase of specific gravity, the alkylene oxidegroup-containing monomer represented by formula (I) is used preferablyin an amount of 30 parts by weight or less. Thus, the monomer (I) isused more preferably in an amount of 10 to 30 parts by weight andparticularly preferably 10 to 20 parts by weight, per 100 parts byweight of total monomers.

Another monomer constituting the transparent resin of the presentinvention, namely the polyfunctional (meth)acrylate, is represented bythe formula (II): ##STR2## wherein R⁴ and R⁵ are independently anacryloyl group or a methacryloyl group; and R⁶ and R⁷ are independentlya monovalent hydrocarbon group having 1 to 6 carbon atoms.

The polyfunctional (meth)acrylates represented by the formula (II)include polyfunctional acrylates such as 2,2-dimethyl-1,3-propanedioldiacrylate, 2-methyl-2-ethyl-1,3-propanediol diacrylate,2-methyl-2-isopropyl-1,3-propanediol diacrylate,2-methyl-2-propyl-1,3-propanediol diacrylate,2,2-diethyl-1,3-propanediol diacrylate, 2-ethyl-2-propyl-1,3-propanedioldiacrylate, 2-ethyl-2-isopropyl-1,3-propanediol diacrylate,2-ethyl-2-butyl-1,3-propanediol diacrylate, 2,2-dipropyl-1,3-dioldiacrylate, 2-propyl-2-butyl-1,3-propanediol diacrylate,2,2-dibutyl-1,3-propanediol diacrylate, 2,2-diisopropyl-1,3-propanedioldiacrylate, 2-propyl-2-isopropyl-1,3-propanediol diacrylate,2-methyl-2-phenyl-1,3-propanediol diacrylate,2-ethyl-2-phenyl-1,3-propanediol diacrylate, 2-propyl-2-phenyl-1,3-dioldiacrylate, 2-isopropyl-2-phenyl-1,3-propanediol diacrylate,2,2-diphenyl-1,3-propanediol diacrylate,2-methyl-2-cyclopentyl-1,3-propanediol diacrylate,2-ethyl-2-cyclopentyl-1,3-propanediol diacrylate,2-propyl-2-cyclopentyl-1,3-propanediol diacrylate,2-isopropyl-2-cyclopentyl-1,3-propanediol diacrylate,2,2-dicyclopentyl-1,3-propanediol diacrylate,2-methyl-2-cyclohexyl-1,3-propanediol diacrylate,2-ethyl-2-cyclohexyl-1,3-propanediol diacrylate,2-propyl-2-cyclohexyl-1,3-propanediol diacrylate,2-isopropyl-2-cyclohexyl-1,3-propanediol diacrylate,2,2-dicyclohexyl-1,3-propanediol diacrylate and the like;

polyfunctional methacrylates such as 2,2-dimethyl-1,3-propanedioldimethacrylate, 2-methyl-2-ethyl-1,3-propanediol dimethacrylate,2-methyl-2-isopropyl-1,3-propanediol dimethacrylate,2-methyl-2-propyl-1,3-propanediol dimethacrylate,2,2-diethyl-1,3-propanediol dimethacrylate,2-ethyl-2-propyl-1,3-propanediol dimethacrylate,2-ethyl-2-isopropyl-1,3-propanediol dimethacrylate,2-ethyl-2-butyl-1,3-propanediol dimethacrylate,2,2-dipropyl-1,3-propanediol dimethacrylate,2-propyl-2-butyl-1,3-propanediol dimethacrylate,2,2-dibutyl-1,3-propanediol dimethacrylate,2,2-diisopropyl-1,3-propanediol dimethacrylate,2-propyl-2-isopropyl-1,3-propanediol dimethacrylate,2-methyl-2-phenyl-1,3-propanediol dimethacrylate,2-ethyl-2-phenyl-1,3-propanediol dimethacrylate,2-propyl-2-phenyl-1,3-propanediol dimethacrylate,2-isopropyl-2-phenyl-1,3-propanediol dimethacrylate,2,2-diphenyl-1,3-propanediol dimethacrylate,2-methyl-2-cyclopentyl-1,3-propanediol dimethacrylate,2-ethyl-2-cyclopentyl-1,3-propanediol dimethacrylate,2-propyl-2-cyclopentyl-1,3-propanediol dimethacrylate,2-isopropyl-2-cyclopentyl-1,3-propanediol dimethacrylate,2,2-dicyclopentyl-1,3-propanediol dimethacrylate,2-methyl-2-cyclohexyl-1,3-propanediol dimethacrylate,2-ethyl-2-cyclohexyl-1,3-propanediol dimethacrylate,2-propyl-2-cyclohexyl-1,3-propanediol dimethacrylate,2-isopropyl-2-cyclohexyl-1,3-propanediol dimethacrylate,2,2-dicyclohexyl-1,3-propanediol dimethacrylate and the like. Thesemonomers are used either in the form of a single monomer or in the formof a mixture of two or more monomers.

Among the polyfunctional (meth)acrylates represented by the formula(II), polyfunctional acrylates such as 2,2-dimethyl-1,3-propanedioldiacrylate and the like and polyfunctional methacrylates such as2,2-dimethyl-1,3-propanediol dimethacrylate,2-methyl-2-ethyl-1,3-propanediol dimethacrylate,2-methyl-2-isopropyl-1,3-propanediol dimethacrylate,2-methyl-2-propyl-1,3-propanediol dimethacrylate,2,2-diethyl-1,3-propanediol dimethacrylate and the like are preferablefrom the viewpoint of specific gravity and heat resistance and, amongthese preferable monomers, 2,2-dimethyl-1,3-propanediol dimethacrylateis particularly preferred.

The polyfunctional (meth)acrylate represented by the formula (II) isused preferably in an amount of 1 to 95 parts by weight per 100 parts byweight of total monomers. If its amount is smaller than 1 part byweight, heat resistance tends to deteriorate and specific gravity is aptto be too high. If its amount exceeds 95 parts by weight, strength atthe time of boring processing and dyeability are apt to deteriorate andadhesiveness to organosilane type hard coat film is apt to decrease.

For sufficiently improving the heat resistance of composition, it ispreferable to use the polyfunctional (meth)acrylate in an amount of atleast 5 parts by weight per 100 parts by weight of total monomers.Further, for preventing the deterioration in the strength at the time ofboring processing and the dyeability and the decrease in adhesiveness toorganosilane type hard coat film, the polyfunctional (meth)acrylate ispreferably used in an amount of 50 parts by weight of less per 100 partsby weight of total monomers. Thus, the polyfunctional (meth)acrylate(II) is used more preferably in an amount of 10 to 40 parts by weightand particularly preferably in an amount of 10 to 30 parts by weight, onthe same basis as above.

Said "other copolymerizable vinyl monomers" include monofunctionalmonomers and polyfunctional monomers. Concrete examples of themonofunctional monomer include the following:

acrylic esters such as methyl acrylate, ethyl acrylate, propyl acrylate,n-butyl acrylate, i-butyl acrylate, t-butyl acrylate, pentyl acrylate,n-hexyl acrylate, 2-ethylhexyl acrylate, n-octyl acrylate, dodecylacrylate, butoxyethyl acrylate, octadecyl acrylate, phenyl acrylate,benzyl acrylate, naphthyl acrylate, cyclopentyl acrylate, cyclohexylacrylate, trimethylcyclohexyl acrylate, norbornyl acrylate,norbornylmethyl acrylate, isobornyl acrylate, bornyl acrylate, menthylacrylate, phenthyl acrylate, adamantyl acrylate, dimethyladamantylacrylate, tricyclo[5.2.1.0².6 ]deca-8-yl acrylate, tricyclo[5.2.1.0².6]deca-4-methyl acrylate, cyclodecyl acrylate, glycerin monoacrylate andthe like;

methacrylic esters such as methyl methacrylate, ethyl methacrylate,propyl methacrylate, n-butyl methacrylate, i-butyl methacrylate, t-butylmethacrylate, pentyl methacrylate, n-hexyl methacrylate, 2-ethylhexylmethacrylate, n-octyl methacrylate, dodecyl methacrylate, butoxyethylmethacrylate, octadecyl methacrylate, phenyl methacrylate, benzylmethacrylate, naphthyl methacrylate, cyclopentyl methacrylate,cyclohexyl methacrylate, methylcyclohexyl methacrylate,trimethylcyclohexyl methacrylate, norbornyl methacrylate,norbornylmethyl methacrylate, isobornyl methacrylate, bornylmethacrylate, menthyl methacrylate, phenthyl methacrylate, adamantylmethacrylate, dimethyladamantyl methacrylate, tricyclo[5.2.1.0².6]deca-8-yl methacrylate, tricyclo[5.2.1.0².6 ]deca-4-methylmethacrylate, cyclodecyl methacrylate, glycerin monomethacrylate and thelike;

aromatic vinyl compounds such as styrene, α-methylstyrene,α-ethylstyrene, α-fluorostyrene, α-chlorostyrene, α-bromostyrene,fluorostyrene, chlorostyrene, bromostyrene, methylstyrene,methoxystyrene and the like;

N-substituted maleimides such as N-methylmaleimide, N-ethylmaleimide,N-propylmaleimide, N-butylmaleimide, N-cyclohexylmaleimide,N-phenylmaleimide, N-methylphenyl-maleimide, N-chlorophenylmaleimide,N-methoxyphenylmaleimide, N-carboxyphenylmaleimide and the like;

(meth)acrylamides such as acrylamide, methacrylamide,N-dimethylacrylamide, N-diethylacrylamide, N-dimethylmethacrylamide,N-diethylmethacrylamide and the like;

(meth)acrylic acid metallic salts such as calcium acrylate, bariumacrylate, lead acrylate, tin acrylate, zinc acrylate, calciummethacrylate, barium methacrylate, lead methacrylate, tin methacrylate,zinc methacrylate and the like;

unsaturated carboxylic acids such as acrylic acid, methacrylic acid andthe like;

epoxy group-containing vinyl compounds such as glycidyl acrylate,glycidyl methacrylate and the like;

hydroxy group-containing vinyl compounds such as hydroxyethyl acrylate,hydroxyethyl methacrylate and the like; alkoxysilyl group-containingvinyl compounds such as γ-(methacryloxypropyl)-trimethoxysilane and thelike;

vinyl cyanide compounds such as acrylonitrile, methacrylonitrile and thelike; etc. These compounds are used either in the form of a singlecompound or in the form of a mixture of two or more compounds.

Concrete examples of the polyfunctional monomer of the otherpolymerizable vinyl monomers include acrylic esters such as ethyleneglycol diacrylate, glycerin diacrylate, glycerin triacrylate,1,4-butanediol diacrylate, 1,6-hexanediol diacrylate, 1,9-nonanedioldiacrylate, 1,10-decanediol diacrylate, 1,12-dodecanediol diacrylate,1-acryloyl-2-hydroxy-3-acryloylpropane, pentaerythritol tetraacrylate,1,1,1-trimethylolpropane triacrylate, dipentaerythritol hexaacrylate,hexamethylolmelamine hexaacrylate,N,N',N"-tris(2-acryloyloxyethyl)isocyanurate and the like;

methacrylic esters such as ethylene glycol dimethacrylate, glycerindimethacrylate, glycerin trimethacrylate, 1,4-butanediol dimethacrylate,1,6-hexanediol dimethacrylate, 1,9-nonanediol dimethacrylate,1,10-decanediol dimethacrylate, 1,12-dodecanediol dimethacrylate,1-methacryloyl-2-hydroxy-3-methacryloylpropane, pentaerythritoltetramethacrylate, 1,1,1-trimethylolpropane trimethacrylate,dipentaerythritol hexamethacrylate, hexamethylolmelamine hexaacrylate,N,N',N"-tris(2-methacryloyloxyethyl)isocyanurate and the like;

allyl and allylidene compounds such as ethyleneglycolbis-allylcarbonate, diethyleneglycolbis-allyl carbonate,triethyleneglycolbis-allyl carbonate, tetraethylene-glycolbis-allylcarbonate, pentaethyleneglycolbis-allyl carbonate,polypropyleneglycolbis-allyl carbonate, trimethyleneglycolbis-allylcarbonate, 3-hydroxy-propoxypropanolbis-allyl carbonate,glycerinbis-allyl carbonate, triglyceringbis-allyl carbonate, diallylcarbonate, diallylidene-pentaerythritol, triallylidene-sorbitol,diallylidene-2,2,6,6-tetramethylolcyclohexanone,triallylidenehexamethylolmelamine, diallylidene-D-glucose, Bisphenol Adiallyl ether, Bisphenol S diallyl ether, ethyleneglycol diallyl ether,1,1,1-trimethylolpropane triallyl ether, neopentylglycol triallyl ether,allyl acrylate, methallyl acrylate, vinyl acrylate, allyl methacrylate,methallyl methacrylate, vinyl methacrylate, diallyl phthalate (diallylorthophthalate, diallyl isophthalate, diallyl terephthalate, andmixtures of two or more thereof), triallyl isocyanurate;

divinylbenzene; etc. These compounds are used either in the form of asingle compound or in the form of a mixture of two or more compounds.

Among the above-mentioned other copolymerizable vinyl monomers, themonofunctional monomers which are preferable from the viewpoint of hue,strength at the time of boring processing, specific gravity,transparency and heat resistance are methacrylic esters such as methylmethacrylate, ethyl methacrylate, propyl methacrylate, n-butylmethacrylate, i-butyl methacrylate, t-butyl methacrylate, pentylmethacrylate, n-hexyl methacrylate, 2-ethylhexyl methacrylate, n-octylmethacrylate, butoxyethyl methacrylate, phenyl methacrylate, benzylmethacrylate, naphthyl methacrylate, methacrylic esters having a C₅ -C₂₂alicyclic hydrocarbon group in the ester part thereof, acrylic estershaving a C₅ -C₂₂ alicyclic hydrocarbon group in the ester part thereof;aromatic vinyl compounds such as styrene and the like; hydroxygroup-containing vinyl compounds such as hydroxyethyl methacrylate andthe like; alkoxysilyl group-containing vinyl compounds such asγ-(methacryloxypropyl)-trimethoxysilane and the like; etc. and thepolyfunctional monomers which are preferable are straight chain alkyleneglycol diacrylates such as ethylene glycol diacrylate, 1,4-butanedioldiacrylate, 1,6-hexanediol diacrylate and the like and straight chainalkylene glycol dimethacrylates such as allyl methacrylate, methallylmethacrylate, ethylene glycol dimethacrylate, 1,4-butanedioldimethacrylate, 1,6-hexanediol dimethacrylate and the like.

As for the formulation of monomer mixture for producing the transparentresin mentioned above, it is preferable to compound 1 to 30 parts byweight, particularly 10 to 20 parts by weight, of the alkylene oxidegroup-containing monomer represented by the formula (I) with 1 to 39parts by weight, particularly 10 to 30 parts by weight, of thepolyfunctional (meth)acrylate represented by the formula (II), 15 to 60parts by weight, particularly 30 to 50 parts by weight, of styrene and 0to 60 parts by weight, particularly 0 to 30 parts by weight, of othercopolymerizable vinyl monomer so as to give a total amount of 100 partsby weight.

If the amount of styrene is smaller than the above, it is difficult toobtain a high refractive index, particularly to make the refractiveindex higher than 1.54. If the amount of styrene is too large, a lowoptical dispersion is difficult to realize, and particularly an Abbenumber of 35 or higher is difficult to realize, and the hue is apt tobecome yellowish.

If the amount of other copolymerizable vinyl monomer is too large, ahigh refractive index, particularly a refractive index of 1.54 or above,is difficult to maintain, and a low specific gravity, particularly aspecific gravity of 1.15 or below, is difficult to maintain.

As the "other copolymerizable vinyl monomer", methacrylic esters andacrylic esters having C₅ -C₂₂ alicyclic hydrocarbon group in the esterpart thereof are preferable. Examples thereof include methacrylic esterssuch as cyclopentyl methacrylate, cyclohexyl methacrylate,methylcyclohexyl methacrylate, trimethylcyclohexyl methacrylate,norbornyl methacrylate, norbornylmethyl methacrylate, isobornylmethacrylate, bornyl methacrylate, menthyl methacrylate, phenthylmethacrylate, adamantyl methacrylate, dimethyladamantyl methacrylate,dimethyladamantyl methacrylate, tricyclo[5.2.1.0²,6 ]deca-8-ylmethacrylate, tricyclo[5.2.1.0²,6 ]deca-4-methyl methacrylate,cyclodecyl methacrylate and the like and acrylic esters such ascyclopentyl acrylate, cyclohexyl acrylate, methylcyclohexyl acrylate,trimethylcyclohexyl acrylate, norbornyl acrylate, norbornylmethylacrylate, isobornyl acrylate, bornyl acrylate, menthyl acrylate,phenthyl acrylate, adamantyl acrylate, dimethyladamantyl acrylate,tricyclo[5.2.1.0²,6 ]deca-8-yl acrylate, tricyclo[5.2.1.0²,6]deca-4-methyl acrylate, cyclodecyl acrylate and the like. These vinylmonomers are used either in the form of a single monomer or in the formof a mixture of two or more monomers. Of these monomers, cyclohexylmethacrylate, norbornyl methacrylate, norbornylmethyl methacrylate,tricyclo[5.2.1.0²,6 ]deca-8-yl methacrylate and tricyclo[5.2.1.0²,6]deca-4-methyl methacrylate are preferable from the viewpoint ofrefractive index, Abbe number, specific gravity and hue, andtricyclo[5.2.1.0²,6 ]deca-8-yl methacrylate is particularly preferable.

Preferably, the methacrylic esters and acrylic esters having C₅ -C₂₂alicyclic hydrocarbon group in the ester part thereof are used in anamount of 1 to 50 parts by weight based on 100 parts by weight of thetotal monomer. If the amount of said methacrylic or acrylic ester issmaller than 1 part by weight, Abbe number is low, hue is yellowish, andspecific gravity is high. If the amount exceeds 50 parts by weight,strength at the time of boring processing and impact resistance are aptto deteriorate. Thus, it is particularly preferable to use thesemonomers in an amount of 5 to 40 parts by weight per 100 parts by weightof total monomer.

It is preferable to use a hydroxy group-containing vinyl compound or analkoxysilyl group-containing vinyl compound, which are both one of saidother copolymerizable vinyl monomers, in an amount of at least 0.01 partby weight per 100 parts by weight of total monomer, because adhesivenessto organosilane type hard coat film can be improved thereby.

In the production of transparent resin, conventional chain transferagent, mercaptan, dialkyl disulfide, chloroform, carbon tetrachloride orthe like may be used as a molecular weight regulator in thepolymerization process. From the viewpoint of transparency, color andheat resistance of plastic lens, α-methylstyrene dimer is particularlypreferably usable for this purpose. The molecular weight regulator isused in an amount of 0.1 to 10% by weight based on the total monomer. Ifits amount is smaller than 0.1% by weight, there arise various problemssuch as high haze rate, deposition of extraneous matter on the surface,readiness of colorization, decrease in strength, etc. If its amountexceeds 10% by weight, properties such as heat resistance deteriorate.Thus, it is particularly preferable to use the molecular weightregulator in an amount of 0.5 to 5% by weight based on the monomermixture.

In the production of the transparent resin, conventional radicalpolymerization initiators can be used as they are. Examples thereofinclude organic peroxides such as1,1-bis(t-butylperoxy)-3,3,5-trimethylcyclohexane,1,1-bis(t-butylperoxy)cyclohexane,n-butyl-4,4'-bis(t-butylperoxy)-valerate, decanoyl peroxide, lauroylperoxide, benzoyl peroxide, m-toluyl peroxide, diisopropylperoxydicarbonate, di-2-ethylhexylperoxy dicarbonate, di-n-propylperoxydicarbonate, dimethoxyisopropylperoxy dicarbonate, cumylperoxyneodecanoate, t-butylperoxy-2-ethylhexanoate,t-butylperoxy-3,5,5-trimethylhexanoate, di-t-butyl-diperoxyisophthalate, t-butylperoxyisopropyl carbonate and the like; azo typepolymerization initiators such as 2,2'-azobis-(isobutyronltrile),2,2'-azobis(4-methoxy-2,4-dimethylvaleronitrile),2,2'-azobis(2,4-dimethylvaleronitrile), dimethyl-2,2'-azobisisobutyrate,2,2'-azobis(2-methylbutyronitrile),1,1'-azobis(1-cyclohexanecarbonitrile),2-phenylazo-2,4-dimethyl-4-methoxyvaleronitrile,2,2'-azobis(2-methylpropane) and the like; etc. These polymerizationinitiators may be used in combination of two or more.

Preferably, the above-mentioned polymerization initiator is used in anamount ranging from 0.001 to 10 parts by weight per 100 parts by weightof total monomer. If the surface state of the resulting polymer and thepolymerization time are taken into consideration, it is particularlypreferable to use the initiators in an amount of 0.01 to 5 parts byweight per 100 parts by weight of total monomer.

In the production of the transparent resin, curing and forming ispreferably carried out by the method of cast polymerization. Forexample, a monomer mixture containing the molecular weight regulator andpolymerization initiator is poured into a mold made from two sheets ofglass and a gasket, the whole is fixed with spring clips or the like ifdesired, and then the whole is heated to make progress curing andforming. Although the curing temperature varies with the kind ofinitiator, it is usually 15° C. to 120° C. Preferably, thepolymerization is started at a relatively low temperature and thetemperature is elevated after gelation in order to prevent the gasketmaterial from corrosion by monomer mixture. The temperature at which themonomer mixture is gelatinized is preferably 35° C. or below, andparticularly preferably 28° C. or below.

In the production of the transparent resin, the material constitutingthe gasket used in cast polymerization is selected from low-densitypolyethylene, plasticized polyvinyl chloride, ethylene-vinyl acetatecopolymer, ethylene-acrylic ester copolymer, polyolefin type elastomer,polyester type elastomer, polyamide type elastomer and fluorinatedelastomer.

The production of the transparent resin is preferably carried out insuch a manner that nitrogen gas is bubbled until oxygen content in theliquid mixture has been reduced to 1.0 mg/liter or less, and thereafterthe liquid mixture is poured into a glass mold and cured and formed bythe method of cast polymerization, in order to prevent colorization andshorten the induction period. The cured lens having completed the mainpolymerization step and released from the mold is heat-treated at 120°C. for 1 to 2 hours. This heat treatment is preferably carried out in anatmosphere of inert gas in order to prevent colorization. By the castpolymerization process, a lens can be formed.

In putting the transparent resin of the present invention to use, anantioxidant of phosphite type, phenol type, thio ether type or the like,a mold release agent such as aliphatic alcohol, fatty acid ester,phthalic ester, triglyceride, fluorinated surfactant, higher fatty acidmetallic salt or the like, as well as a slipper, a plasticizer, anantistatic agent, an ultraviolet absorber, a flame retardant, a heavymetal inactivator and the like, may be added to the resin for thepurpose of preventing deterioration or improving heat stability andprocessing characteristics. These additives are preferably added in thecourse of polymerization.

The surface of the lens made of the transparent resin of the presentinvention may be coated with an inorganic compound such as MgF₂, SiO₂ orthe like by the method of vacuum vapor deposition, sputtering, ionplating or the like, and a hard coat may be formed on the lens surfacewith an organosilicone compound such as silane coupler or the like, avinyl monomer, a melamine resin, an epoxy resin, a fluorinated resin, asilicone resin or the like; whereby moisture resistance, opticalcharacteristics, chemical resistance, abrasion resistance and defoggingproperty of the lens can be improved.

On the surface of the lens made of the transparent resin (base materialfor a plastic lens), an organosilane type hard coat film or a cured filmof organosilane resin may directly be laminated to make a plastic lens.

Said organosilane resin is an organosilane compound represented by thefollowing formula (III):

    R.sup.8 R.sup.9.sub.a Si(OR.sup.10).sub.3-a                (III)

wherein R⁸ is an organic group containing an epoxy group having 2 to 8carbon atoms, R⁹ is an alkyl group having 1 to 6 carbon atoms, analkenyl group, a halogenated alkyl group or an allyl group, R¹⁰ is ahydrogen atom, an alkyl group having 1 to 4 carbon atoms, analkoxy-alkyl group or an acyl group, and a is 0, 1 or 2; or a partialhydrolyzate thereof. Concrete examples of said organosilane resininclude organosilane compounds such asγ-glycidoxypropyltrimethoxysilane, γ-glycidoxypropyltriethoxysilane,γ-glycidoxypropyl-tris(methoxyethoxy)silane,γ-glycidoxypropylmethyldimethoxy-silane,γ-glycidoxypropylmethyldiethoxysilane and the like, and partialhydrolyzates thereof. As a commercial product, KP64C (trade name,manufactured by Shin-Etsu Chemical Co., Ltd.) can be referred to.

The organosilane resin mentioned above to which its 10 to 80% by weightof a colloidal solution prepared by dispersing inorganic fineparticulate material such as antimony oxide sol, silica sol, titaniasol, alumina sol or the like in water or an alcohol such as methanol,ethanol, isobutanol, diacetone alcohol or the like has previously beenadded is directly applied to the surface of the base material of plasticlens obtained above, and cured with heating at 50° to 140° C., whereby ahard coat layer can be formed. If desired, a primer layer may be formedbetween the surface of plastic lens and the hard coat layer or thesurface of base material of plastic lens may be subjected to a surfacetreatment such as plasma treatment or the like. However, the basematerial of plastic lens obtained according to the present inventiondoes not always require these pre-treatments.

As the inorganic fine particulate material, those having a particlediameter of 1 to 100 μm are preferable. Colloidal solutions dispersed inwater or organic solvent which are commercially available usually mayalso be used.

If desired, a curing catalyst such as aluminum chelate, perchloric acid,perchlorates (for example, ammonium perchlorate, aluminum perchlorateand the like), alkali metal salts (for example, sodium acetate,potassium propionate and the like), quaternary ammonium salts (forexample, tetramethylammonium hydroxide and the like), etc. may be addedto the organosilane resin.

The lens made of the above-mentioned transparent resin can be dyed bydipping it in water in which a dye is dispersed.

As said dye, those conventionally used in this field of industry may beused directly. Examples thereof include C. I. Disperse Red 13, 56 and112; C. I. Disperse Yellow 3, 7, 31, 42, 54 and 198; C. I. Disperse Blue1, 3, 5, 54, 56 and 197; etc.

In carrying out the dyeing, dyeing assistants such as ph regulator,wetting agent, surfactant, dispersion promotor, antifoaming agent andthe like may be added, whereby color depth and uniformity of dyeing canbe improved.

In carrying out the dyeing, an aromatic compound such as benzyl alcohol,phenol, butyl benzoate, methyl salicylate and the like, an aliphaticalcohol such as 1-butanol, ethyl cellosolve, cyclopentanol and the like,or an aliphatic ester such as butyl cellosolve acetate, methylacetoacetate and the like may be added as a carrier, whereby color depthof dyeing can be improved.

Next, the present invention is explained more concretely with referenceto examples, wherein parts and percents are by weight unless otherwisespecified.

EXAMPLES 1 to 16

To a liquid mixture of the formulation shown in Table 1 weresuccessively added 1.0 part of diisopropylperoxy dicarbonate and 0.1part of t-butylperoxy isopropyl carbonate. After thoroughly stirring theresulting mixture, the mixture was poured into a mold constructed fromtwo glass sheets and a gasket, gelled at 25° C., and heated to 90° C.The cured lens was released from the mold, heat-treated at 120° C. for 2hours, and cooled to room temperature. Then, the lens was coated with anorganosilane type hard coat agent (trade name "KP64C", manufactured byShin-Etsu Chemical Co., Ltd.) by dipping method, and heated first atroom temperature for 30 minutes, subsequently at 90° C. for 30 minutes,and finally at 120° C. for one hour to cure the hard coat film.

Comparative Examples 1 to 11

To a liquid mixture of the formulation shown in Table 2 weresuccessively added 1.0 part of diisopropylperoxy dicarbonate and 0.1part of t-butylperoxy isopropyl carbonate. After thoroughly stirring theresulting mixture, the mixture was poured into a mold constructed fromtwo glass sheets and a gasket, gelled at 25° C., and heated to 90° C.The cured lens was released from the mold, heat treated at 120° C. for 2hours, and cooled to room temperature. Then, the lens was coated with anorganosilane type hard coat agent (trade name "KP64C", manufactured byShin-Etsu Chemical Co., Ltd.) by dipping method and heated first at roomtemperature for 30 minutes, subsequently at 90° C. for 30 minutes andfinally at 120° C. for one hour to cure the hard coat layer.

On the lenses obtained in Examples 1 to 16 and Comparative Examples 1 to11, refractive index, Abbe number, specific gravity, heat resistance,transparency, tensile strength in boring, hue, adhesiveness to hard coatand dyeability were evaluated. The results were as shown in Tables 3 and4.

The properties were evaluated according to the following methods.

Refractive Index and Abbe Number: Measured with Abbe refractometer(manufactured by Atago Co.) at 20° C. The values shown in Table 1 arethose measured with D line (589.3 nm).

Specific Gravity: Measured by the water substitution method.

Heat Resistance: Ts (softening temperature), which is a temperature atwhich a needle begins to penetrate, and penetration of needle (thermaldeformation) are measured with TMA (Thermal Mechanical Analyzer,manufactured by Seiko Electronics Co.).

Haze rate (transparency): Measured according to ASTM D 1003 on a lenshaving a central thickness of 5 mm. A smaller value means a moreexcellent transparency.

Tensile Strength in Boring: Holes having a diameter of 2.0 mm areperforated in both terminals of a lens having a thickness of 2 mm, boltsare introduced into the holes, and the bolts are stretched by means oftensile tester to measure strength.

Hue: YI value (yellowing index) is measured with Color Difference Meter(manufactured by Nippon Denshoku Co.).

Adhesiveness to Hard Coat: Eleven lines are carved in both thelongitudinal and lateral directions on a hard coat film by means of aknife. After attaching a cellophane tape (manufactured by Nichiban Co.)thereto, the cellophane tape is quickly peeled off, and the number ofsquares left unpeeled is counted.

∘: 100/100 to 80/100

x: 0/100 to 20/100

Dyeability: In one liter of pure water are dissolved 5 g of a dye, 2 mlof a dyeing assistant and 10 g of benzyl methacrylate. After heating thesolution to 90° C., a lens is dipped in the solution for 15 minutes forthe sake of dyeing. The extent of dyeing after the dyeing process isevaluated in five stages and expressed by the following marks:

5: Very well dyeable,

4: Well dyeable,

3: Somewhat dyeable,

2: Slightly dyeable,

1: Hardly dyeable.

In the tables shown below, meanings of the marks are as follows:

ST styrene

MMA: methyl methacrylate

TCDMA: tricyclo[5.2.1.0².6 ]deca-8-yl methacrylate

NPDM: 2,2-dimethyl-1,3-propanediol dimethacrylate

NPDA: 2,2-dimethyl-1,3-propanediol diacrylate,

9EGDM: nonaethylene glycol dimethacrylate

14EGDM: tetradecaethylene glycol dimethacrylate

9EGMM: nonaethylene glycol monomethacrylate

HEMA: 2-hydroxyethyl methacrylate

EGDM: ethylene glycol dimethacrylate

4EGDM: tetraethylene glycol dimethacrylate

4EGDM: tetraethylene glycol dimethacrylate

DDDM: 1,10-decanediol dimethacrylate

α-MSD: α-methylstyrene dimer

NOM: n-octylmercaptan

provided that the amounts of α-MSD and NOM are expressed in terms of %by weight based on total monomer, and

CHMA: cyclohexyl methacrylate.

                                      TABLE 1                                     __________________________________________________________________________    Formulation of liquid mixture                                                 Monomer composition (%) by wt.)               α-MSD                     ST      MMA TCDMA                                                                              NPDM                                                                              NPDA                                                                              9EGDM                                                                              14EGDM                                                                              9EGMM                                                                              HEMA (% by wt.)                      __________________________________________________________________________    Example 1                                                                           50                                                                              15  --   20  --  15   --    --   --   1.0                             Example 2                                                                           50                                                                              15  --   20  --  --   15    --   --   1.0                             Example 3                                                                           50                                                                              15  --   --  20  15   --    --   --   1.0                             Example 4                                                                           50                                                                              15  --   --  20  --   15    --   --   1.0                             Example 5                                                                           50                                                                              --  15   20  --  15   --    --   --   1.0                             Example 6                                                                           50                                                                              --  15   20  --  --   15    --   --   1.0                             Example 7                                                                           50                                                                              --  15   --  20  15   --    --   --   1.0                             Example 8                                                                           50                                                                              --  15   --  20  --   15    --   --   1.0                             Example 9                                                                           50                                                                              --  15   20  --  --   15    --   --   NOM1.0                          Example 10                                                                          50                                                                              --  15   20  --  --   15    --   --   --                              Example 11                                                                          50                                                                              --  14   20  --  --   15    --   1.0  1.0                             Example 12                                                                          41                                                                              24  --   20  --  15   --    --   --   1.0                             Example 13                                                                          41                                                                              24  --   20  --  --   15    --   --   1.0                             Example 14                                                                          41                                                                              --  24   20  --  15   --    --   --   1.0                             Example 15                                                                          41                                                                              --  24   20  --  --   15    --   --   1.0                             Example 16                                                                          50                                                                              15  20   --  --  --   --    15   --   1.0                             __________________________________________________________________________

                                      TABLE 2                                     __________________________________________________________________________    Formulation of liquid mixture                                                        Monomer composition (%) by wt.)     α-MSD                               ST                                                                              MMA TCDMA                                                                              NPDM                                                                              EGDM 4EGDM                                                                              DDDM 14EGMM                                                                              (% by wt.)                         __________________________________________________________________________    Comparative                                                                   Example 1                                                                            50                                                                              30  --   --  20   --   --   --    1.0                                Example 2                                                                            50                                                                              --  30   --  20   --   --   --    1.0                                Example 3                                                                            50                                                                              --  30   20  --   --   --   --    1.0                                Example 4                                                                            50                                                                              --  30   --  --   --   20   --    1.0                                Example 5                                                                            50                                                                              --  30   --  --   --   --   20    1.0                                Example 6                                                                            50                                                                              15  --   --  20   --   --   15    1.0                                Example 7                                                                            50                                                                              15  --   --  --   --   20   15    1.0                                Example 8                                                                            50                                                                              --  15   --  20   --   --   15    1.0                                Example 9                                                                            50                                                                              --  15   --  --   --   20   15    1.0                                Example 10                                                                           50                                                                              --  15   20  --   --   15   --    1.0                                Example 11                                                                           50                                                                              --  15   20  --   15   --   --    1.0                                __________________________________________________________________________

                                      TABLE 3                                     __________________________________________________________________________    Results of evaluation                                                         Refractive  Abbe Specific                                                                              Penetration                                                                         Haze       Adhesive-                                                                           Dye-                          index       number                                                                             gravity                                                                            Ts of needle                                                                           rate                                                                             Strength                                                                           YI ness to                                                                             ability                       (-)         (-)  (g/cm.sup.3)                                                                       (°C.)                                                                     (μm)                                                                             (%)                                                                              (kgf)                                                                              (%)                                                                              hard coat                                                                           (1-5)                         __________________________________________________________________________    Example 1                                                                           1.55  41   1.11 121                                                                              1     0.5                                                                              15   1.2                                                                              ◯                                                                       3                             Example 2                                                                           1.55  41   1.11 116                                                                              1     0.5                                                                              20   1.1                                                                              ◯                                                                       5                             Example 3                                                                           1.55  41   1.11 109                                                                              2     0.5                                                                              15   1.2                                                                              ◯                                                                       4                             Example 4                                                                           1.55  41   1.11 106                                                                              3     0.5                                                                              20   1.1                                                                              ◯                                                                       5                             Example 5                                                                           1.55  41   1.10 122                                                                              1     0.5                                                                              15   1.2                                                                              ◯                                                                       3                             Example 6                                                                           1.55  41   1.10 117                                                                              1     0.5                                                                              20   1.1                                                                              ◯                                                                       5                             Example 7                                                                           1.55  41   1.10 110                                                                              2     0.5                                                                              15   1.2                                                                              ◯                                                                       4                             Example 8                                                                           1.55  41   1.10 106                                                                              3     0.5                                                                              20   1.1                                                                              ◯                                                                       5                             Example 9                                                                           1.55  41   1.10 117                                                                              1     0.5                                                                              20   1.3                                                                              ◯                                                                       5                             Example 10                                                                          1.55  41   1.10 120                                                                              1     0.5                                                                              20   1.3                                                                              ◯                                                                       5                             Example 11                                                                          1.55  41   1.10 120                                                                              1     0.5                                                                              20   1.1                                                                              ◯                                                                       5                             Example 12                                                                          1.55  42   1.12 122                                                                              1     0.5                                                                              15   1.2                                                                              ◯                                                                       3                             Example 13                                                                          1.55  42   1.12 116                                                                              1     0.5                                                                              20   1.1                                                                              ◯                                                                       5                             Example 14                                                                          1.55  42   1.11 123                                                                              1     0.5                                                                              15   1.1                                                                              ◯                                                                       3                             Example 15                                                                          1.55  42   1.11 119                                                                              1     0.5                                                                              20   1.0                                                                              ◯                                                                       5                             Example 16                                                                          1.55  41   1.10 110                                                                              25    0.5                                                                              12   1.3                                                                              ◯                                                                       5                             __________________________________________________________________________

                                      TABLE 4                                     __________________________________________________________________________    Results of evaluation                                                                Refractive                                                                          Abbe Specific                                                                              Penetration                                                                         Haze       Adhesive-                                                                           Dye-                                index number                                                                             gravity                                                                            Ts of needle                                                                           rate                                                                             Strength                                                                           YI ness to                                                                             ability                             (-)   (-)  (g/cm.sup.3)                                                                       (°C.)                                                                     (μm)                                                                             (%)                                                                              (kgf)                                                                              (%)                                                                              hard coat                                                                           (1-5)                        __________________________________________________________________________    Comparative                                                                   Example 1                                                                            1.55  41   1.15 147                                                                              5     0.5                                                                              5    1.3                                                                              x     1                            Example 2                                                                            1.55  41   1.13 148                                                                              5     0.5                                                                              5    1.3                                                                              x     1                            Example 3                                                                            1.55  41   1.09 127                                                                              20    0.5                                                                              5    1.2                                                                              x     1                            Example 4                                                                            1.55  41   1.11  86                                                                              32    0.5                                                                              5    1.2                                                                              x      5*                          Example 5                                                                            1.55  41   1.13  88                                                                              48    0.5                                                                              20   1.3                                                                              ◯                                                                        5*                          Example 6                                                                            1.55  41   1.16 137                                                                              1     0.5                                                                              15   1.3                                                                              ◯                                                                       2                            Example 7                                                                            1.55  41   1.13  68                                                                              16    0.5                                                                              12   1.3                                                                              ◯                                                                        5*                          Example 8                                                                            1.55  41   1.16 137                                                                              1     0.5                                                                              20   1.3                                                                              ◯                                                                       3                            Example 9                                                                            1.55  41   1.13  62                                                                              17    0.5                                                                              12   1.3                                                                              ◯                                                                        5*                          Example 10                                                                           1.55  41   1.10 113                                                                              1     0.5                                                                              5    1.1                                                                              x     1                            Example 11                                                                           1.55  41   1.11 131                                                                              1     0.5                                                                              5    1.3                                                                              ◯                                                                       1                            __________________________________________________________________________     *: The lens was discolored during the dyeing process.                    

Since the transparent resin of the present invention is excellent intransparency, strength at the time of boring and dyeability, low inspecific gravity and excellent in adhesiveness to organosilane resin, itcan directly be coated with cured film of an organosilane resin(organosilane type hard coat film) without surface treatment. Further, atransparent resin of the present invention of which monomer formulationis modified exhibits, in addition to the effect of the transparent resinitself, a high refractive index, a low dispersibility (high Abbenumber), an excellent hue and a high heat resistance. Further, since thetransparent resin obtained according to the process of the presentinvention is excellent in transparency, strength at the time of boringand dyeability, low in specific gravity and excellent in theadhesiveness to organosilane resin, it can directly be coated with acured film of an organosilane resin (organosilane type hard coat film)without surface treatment. Further, a transparent resin of which monomerformulation is modified exhibits, in addition to the effect of thetransparent resin itself, a high refractive index, a low dispersibility(high Abbe number), an excellent hue and a high heat resistance.

Further, since the plastic lens of the present invention is excellent intransparency, strength at the time of boring and dyeability, low inspecific gravity and excellent in adhesiveness to organosilane resin, itcan directly be coated with a cured film of organosilane resin(organosilane type hard coat film) without surface treatment. Further,by modifying the formulation of monomer, there can be provided a plasticlens exhibiting, in addition to the above-mentioned effects, a highrefractive index, a low dispersibility (high Abbe number), an excellenthue and a high heat resistance.

What is claimed is:
 1. A transparent resin comprising, as constituentcomponents of the resin molecules, a polymerizable monomer mixtureobtained by compounding 1 to 80 parts by weight of an alkylene oxidegroup-containing monomer represented by the formula (I):

    R.sup.1 --O--(R.sup.2 O).sub.n --R.sup.3                   (I)

wherein R¹ is an acryloyl group or a methacryloyl group; R² is analkylene group having 1 to 5 carbon atoms; R³ is a hydrogen atom, anacryloyl group, a methacryloyl group or a monovalent hydrocarbon groupother than mentioned above and having 1 to 40 carbon atoms; and n is aninteger of 9 to 50; 1 to 95 parts by weight of a polyfunctional(meth)acrylate represented by the formula (II): ##STR3## wherein R⁴ andR⁵ are independently an acryloyl group or a methacryloyl group; and R⁶and R⁷ are independently a monovalent hydrocarbon group having 1 to 6carbon atoms; and 0 to 90 parts by weight of other copolymerizable vinylmonomer so as to give a total amount of 100 parts by weight.
 2. Atransparent resin according to claim 1, wherein said polymerizablemonomer mixture comprises, as constituent components of the resinmolecules, 1 to 30 parts by weight of the alkylene oxidegroup-containing monomer represented by the formula (I), 1 to 39 partsby eight of the polyfunctional (meth)acrylate represented by the formula(II), 15 to 60 parts by weight of styrene and 0 to 60 parts by weight ofother copolymerizable vinyl monomer so as to give a total amount of 100parts by weight.
 3. A transparent resin according to claim 1, whereinthe alkylene oxide group-containing monomer of the formula (I) is atleast one polyfunctional monomer or monofunctional monomer having anacryloyl group or a methacryloyl group as R³.
 4. A transparent resinaccording to claim 3, wherein the polyfunctional monomer is at least onemember selected from the group consisting of polymethylene glycoldiacrylates, polymethylene glycol dimethacrylates, polyethylene glycoldiacrylates, polyethylene glycol dimethacrylates, polypropylene glycoldiacrylates, polypropylene glycol dimethacrylates, polybutylene glycoldiacrylates, polybutylene glycol dimethacrylates, polyethylene glycolpolypropylene glycol diacrylates, polyethylene glycol propylene glycoldimethacrylates, polyethylene glycol polybutylene glycol diacrylates,and polyethylene glycol polybutylene glycol dimethacrylates.
 5. Atransparent resin according to claim 1, wherein the polyfunctional(meth)acrylate of the formula (II) is 2,2-dimethyl-1,3-propanedioldiacrylate, 2,2-dimethyl-1,3-propanediol dimethacrylate,2-methyl-2-ethyl-1,3-propanediol dimethacrylate,2-methyl-2-isopropyl-1,3-propanediol dimethacrylate,2-methyl-2-propyl-1,3-propanediol dimethacrylate,2,2-diethyl-1,3-propanediol dimethacrylate, or a mixture thereof.
 6. Atransparent resin according to claim 1, wherein the alkylene oxidegroup-containing monomer of the formula (I) is tetradecaethylene glycoldiacrylate or tetradecaethylene glycol dimethacrylate.
 7. A transparentresin according to claim 2, wherein the alkylene oxide group-containingmonomer of the formula (I) is at least one polyfunctional monomer ormonofunctional monomer having an acryloyl group or a methacryloyl groupas R³.
 8. A transparent resin according to claim 7, wherein thepolyfunctional monomer is at least one member selected from the groupconsisting of polymethylene glycol diacrylates, polymethylene glycoldimethacrylates, polyethylene glycol diacrylates, polyethylene glycoldimethacrylates, polypropylene glycol diacrylates, polypropylene glycoldimethacrylates, polybutylene glycol diacrylates, polybutylene glycoldimethacrylates, polyethylene glycol polypropylene glycol diacrylates,polyethylene glycol propylene glycol dimethacrylates, polyethyleneglycol polybutylene glycol diacrylates, and polyethylene glycolpolybutylene glycol dimethacrylates.
 9. A transparent resin according toclaim 2 wherein the polyfunctional (meth)acrylate of the formula (II) is2,2-dimethyl-1,3-propanediol diacrylate, 2,2-dimethyl-1,3-propanedioldimethacrylate, 2-methyl-2-ethyl-1,3-propanediol dimethacrylate,2-methyl-2-isopropyl-1,3-propanediol dimethacrylate,2-methyl-2-propyl-1,3-propanediol dimethacrylate,2,2-diethyl-1,3-propanediol dimethacrylate, or a mixture thereof.
 10. Atransparent resin according to claim 2, wherein the alkylene oxidegroup-containing monomer of the formula (I) is tetradecaethylene glycoldiacrylate or tetradecaethylene glycol dimethacrylate.